An Overview of Solid Supported Palladium and Nickel Catalysts for C-C Cross Coupling Reactions

Author(s): Jaishri Chopra, Ajay K. Goswami, Prabhat K. Baroliya*

Journal Name: Mini-Reviews in Organic Chemistry

Volume 17 , Issue 5 , 2020


DOI : 10.2174/1570193X16666190617160339

  Journal Home
Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


Abstract:

Solid supported catalysts have been of considerable interest in organic synthesis for the last few years. Solid support provides an efficient heterogeneous catalytic system owing to facile recovery and extensive recycling by simple filtration because of possessing 3-R approach (Recoverable, Robust and Recyclable) and makes solid supported catalyst more appealing nowadays. In view of the high cost and shortage of furthermost used palladium catalyst, its recovery and recycling are vital issues for any large-scale application which are being overcome by using solid supported catalytic systems. Therefore, a variety of inorganic and organic solid-supported catalytic systems have been developed so far in order to address these challenges. This review attempts highlight a number of solid supported catalytic systems in the pro-active area of widely used C-C cross coupling reactions.

Keywords: C-C coupling reaction, catalyst, heterogeneous, organic synthesis, palladium, solid support.

[1]
Soderberg, B.C.G. Transition metals in organic synthesis: Highlights for the year 2003. Coord. Chem. Rev., 2006, 250, 300-387.
[http://dx.doi.org/10.1016/j.ccr.2005.03.033]
[2]
Davies, P.W. Organometallics: Transition metals in organic synthesis. Annu. Rep. Prog. Chem., 2009, Sect.105(B), 93-112.
[3]
Morimoto, N.; Morioku, K.; Suzuki, H.; Nakai, Y.; Nishina, Y. Carbocatalytic reductive coupling reactions via electron transfer from graphene to aryldiazonium salt. Chem. Commun. (Camb.), 2017, 53(53), 7226-7229.
[http://dx.doi.org/10.1039/C7CC02337E] [PMID: 28470320]
[4]
Arisawa, M. Synthesis of organosulfides using transition-metal-catalyzed substitution reactions: to construct exergonic reactions employing metal inorganic, organic co-substrate/co-product methods. Tetrahedron Lett., 2014, 55(23), 3391-3399.
[http://dx.doi.org/10.1016/j.tetlet.2014.04.081]
[5]
Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J. Transition metal-catalyzed carbocyclizations in organic synthesis. Chem. Rev., 1996, 96(2), 635-662.
[http://dx.doi.org/10.1021/cr950065y] [PMID: 11848768]
[6]
Chen, X.; Engle, K.M.; Wang, D.H.; Yu, J.Q. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: Versatility and practicality. Angew. Chem. Int. Ed. Engl., 2009, 48(28), 5094-5115.
[http://dx.doi.org/10.1002/anie.200806273] [PMID: 19557755]
[7]
Biajoli, A.F.P.; Schwalm, C.S.; Limberger, J.; Claudino, T.S.; Monteiro, A.L. Recent progress in the use of Pd-catalyzed C-C cross-coupling reactions in the synthesis of pharmaceutical compounds. J. Brazil. Chem. Soc., 2014, 25(12), 2186-2214.
[http://dx.doi.org/10.5935/0103-5053.20140255]
[8]
Magano, J.; Dunetz, J.R. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals. Chem. Rev., 2011, 111(3), 2177-2250.
[http://dx.doi.org/10.1021/cr100346g] [PMID: 21391570]
[9]
Torborg, C.; Beller, M. Recent applications of palladium-catalyzed coupling reactions in the pharmaceutical, agrochemical and fine chemical industries. Adv. Synth. Catal., 2009, 351, 3027-3043.
[http://dx.doi.org/10.1002/adsc.200900587]
[10]
Roughley, S.D.; Jordan, A.M. The medicinal chemist’s toolbox: An analysis of reactions used in the pursuit of drug candidates. J. Med. Chem., 2011, 54(10), 3451-3479.
[http://dx.doi.org/10.1021/jm200187y] [PMID: 21504168]
[11]
Agar, S.; Gunkara, O.T. The latest advancements in the acylation reactions via cross-dehydrogenative coupling and/or metal catalysts. J. Turkish Chem. Soc., 2018, 5(1), 247-268.
[12]
Lima, C.F.R.A.C.; Rodrigues, A.S.M.C.; Silva, V.L.M.; Silva, A.M.S.; Santos, L.M.N.B.F. Role of the base and control of selectivity in the Suzuki-Miyaura cross-coupling reaction. ChemCatChem, 2014, 6, 1291-1302.
[http://dx.doi.org/10.1002/cctc.201301080]
[13]
Heck, R.F. Palladium catalysed vinylation of organic halides. Org. React., 1982, 27, 345-390.
[14]
Nicolaou, K.C.; Bulger, P.G.; Sarlah, D. Palladium-catalyzed cross-coupling reactions in total synthesis. Angew. Chem. Int. Ed. Engl., 2005, 44(29), 4442-4489.
[http://dx.doi.org/10.1002/anie.200500368] [PMID: 15991198]
[15]
Reetz, M.T.; de Vries, J.G.; Johannes, G. Ligand-free Heck reactions using low Pd-loading. Chem. Commun. (Camb.), 2004, (14), 1559-1563.
[http://dx.doi.org/10.1039/b406719n] [PMID: 15263925]
[16]
Darmawan, A.; Karlina, L.; Astuti, Y.; Wang, D.K.; Motuzas, J.; Costa, J.C.D. Interlayer free nickel doped silica membranes for desalination. Mater. Sci. Eng., 2017, 172.
[17]
Hazari, N.; Melvin, P.R.; Beromi, M.M. Well-defined nickel and palladium precatalysts for cross-coupling. Nat. Rev., 2017, 1, 0025.
[18]
Iwasaki, T.; Fukuoka, A.; Yokoyama, W.; Min, X.; Hisaki, I.; Yang, T.; Ehara, M.; Kuniyasu, H.; Kambe, N. Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents in the presence of 1,3-butadiene: mechanistic studies of four-component coupling and competing cross-coupling reactions. Chem. Sci. (Camb.), 2018, 9(8), 2195-2211.
[http://dx.doi.org/10.1039/C7SC04675H] [PMID: 29719693]
[19]
Karimi, B.; Akhavan, P.F. A study on applications of N-substituted main-chain NHC-palladium polymers as recyclable self-supported catalysts for the Suzuki-Miyaura coupling of aryl chlorides in water. Inorg. Chem., 2011, 50(13), 6063-6072.
[http://dx.doi.org/10.1021/ic2000766] [PMID: 21648445]
[20]
Jadhav, S.; Kumbhar, A.; Salunkhe, R. Palladium supported on silica-chitosan hybrid material (Pd-CS@SiO2) for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions. Appl. Organomet. Chem., 2015, 29(6), 339-345.
[http://dx.doi.org/10.1002/aoc.3290]
[21]
Yuxia, L.; Jun, J.; Haohan, T.; Yanan, S.; Jingchao, T. Efficient polymer-supported pd catalysts for the Heck reaction. Chin. J. Chem., 2010, 28, 967-973.
[http://dx.doi.org/10.1002/cjoc.201090179]
[22]
Dalal, M.K. Green chemistry on solid support. APCBEE Procedia, 2012, 3, 276-280.
[http://dx.doi.org/10.1016/j.apcbee.2012.06.082]
[23]
Sharma, D.; Kumar, D.; Shil, A.K.; Guha, N.R.; Das, P. Solid supported palladium(0) nano/microparticle: A ligand-free efficient recyclable heterogeneous catalyst for mono- and b,b-double-Heck reaction. Tetrahedron Lett., 2012, 53, 7044-7051.
[http://dx.doi.org/10.1016/j.tetlet.2012.10.062]
[24]
Astruc, D. Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view. Inorg. Chem., 2007, 46(6), 1884-1894.
[http://dx.doi.org/10.1021/ic062183h] [PMID: 17348719]
[25]
Yin, L.; Liebscher, J. Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts. Chem. Rev., 2007, 107(1), 133-173.
[http://dx.doi.org/10.1021/cr0505674] [PMID: 17212474]
[26]
Albilali, R.; Douthwaite, M.; Heb, Q.; Taylor, S.H. The selective hydrogenation of furfural over supported palladium nanoparticle catalysts prepared by sol-immobilisation: Effect of catalyst support and reaction conditions. Catal. Sci. Technol., 2018, 8, 252-267.
[http://dx.doi.org/10.1039/C7CY02110K]
[27]
Ghaedi, M.; Rezakhani, M.; Khodadoust, S.; Niknam, K.; Soylak, M. The solid phase extraction of some metal ions using palladium nanoparticles attached to silica gel chemically bonded by silica bonded N-propylmorpholine as new sorbent prior to their determination by flame atomic absorption spectroscopy. Scientific- World Journal, 2012, 2012, 764195
[http://dx.doi.org/10.1100/2012/764195] [PMID: 22666150]
[28]
Sabermahani, F.; Saeidi, M.; Sharifzade, V. Removal of Nickel (ii) and palladium (ii) from surface waters. Bull. Chem. Soc. Ethiop., 2013, 27(1), 15-23.
[29]
Kasaini, H.; Kekana, P.T.; Saghti, A.A.; Bolton, K. Adsorption characteristics of cobalt and nickel on oxalate-treated activated carbons in sulphate media. World Acad. Sci. Eng. Technol., 2013, 76, 707-721.
[30]
Karimi, B.; Elhamifar, D.; Clark, J.H.; Hunt, A.J. Ordered mesoporous organosilica with ionic-liquid framework: An efficient and reusable support for the palladium-catalyzed Suzuki-Miyaura coupling reaction in water. Chemistry, 2010, 16(27), 8047-8053.
[http://dx.doi.org/10.1002/chem.201000538] [PMID: 20512825]
[31]
Redón, R.; Peña, N.G.G.; Crescencio, F.R. Leaching in metal nanoparticle catalysis. Recent Pat. Nanotechnol., 2014, 8(1), 31-51.
[http://dx.doi.org/10.2174/1872210508999140130122644] [PMID: 24635207]
[32]
Kumbhar, A. Palladium catalyst supported on zeolite for cross-coupling reactions: An overview of recent advances. Top. Curr. Chem. (Cham), 2017, 375(1), 2.
[http://dx.doi.org/10.1007/s41061-016-0084-5] [PMID: 27928737]
[33]
Liew, K.H.; Loh, P.L.; Juan, J.C.; Yarmo, M.A.; Yusop, R.M. QuadraPure-supported palladium nanocatalysts for microwave-promoted Suzuki cross-coupling reaction under aerobic condition. ScientificWorldJournal, 2014, 2014, 796196
[http://dx.doi.org/10.1155/2014/796196] [PMID: 25054185]
[34]
Vries, D.; Johannes, G. The Heck reaction in the production of fine chemicals. Can. J. Chem., 2001, 79, 1086-1092.
[http://dx.doi.org/10.1139/v01-033]
[35]
Gupta, S.S.; Bhattacharyya, K.G. Adsorption of metal ions by clays and inorganic solids. RSC Advances, 2014, 4, 28537-28586.
[http://dx.doi.org/10.1039/C4RA03673E]
[36]
Choudary, B.M.; Madhi, S.; Chowdari, N.S.; Kantam, M.L.; Sreedhar, B. Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes. J. Am. Chem. Soc., 2002, 124(47), 14127-14136.
[http://dx.doi.org/10.1021/ja026975w] [PMID: 12440911]
[37]
Astruc, D.; Lu, F.; Aranzaes, J.R. Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. Engl., 2005, 44(48), 7852-7872.
[http://dx.doi.org/10.1002/anie.200500766] [PMID: 16304662]
[38]
Corbet, J.P.; Mignani, G. Selected patented cross-coupling reaction technologies. Chem. Rev., 2006, 106(7), 2651-2710.
[http://dx.doi.org/10.1021/cr0505268] [PMID: 16836296]
[39]
Fan, J.; Gao, Y. Nanoparticle-supported catalysts and catalytic reactions - A mini-review. J. Exp. Nanosci., 2006, 1(4), 457-475.
[http://dx.doi.org/10.1080/17458080601067708]
[40]
Mori, K.; Hanafusa, A.; Che, M.; Yamashita, H. In situ generation of active pd nanoparticles within a macroreticularacidic resin: Efficient catalyst for the direct synthesis of hydrogen peroxide. J. Phys. Chem. Lett., 2010, 1, 1675-1678.
[http://dx.doi.org/10.1021/jz100509x]
[41]
Schauermann, S.; Nilius, N.; Shaikhutdinov, S.; Freund, H.J. Nanoparticles for heterogeneous catalysis: new mechanistic insights. Acc. Chem. Res., 2013, 46(8), 1673-1681.
[http://dx.doi.org/10.1021/ar300225s] [PMID: 23252628]
[42]
Xia, Y.; Yang, H.; Campbell, C.T. Nanoparticles for catalysis. Acc. Chem. Res., 2013, 46(8), 1671-1672.
[http://dx.doi.org/10.1021/ar400148q] [PMID: 23957601]
[43]
Nyangasi, L.O.; Andala, D.M.; Onindo, C.O.; Ngila, J.C.; Makhubela, B.C.E.; Ngigi, E.M. Preparation and characterization of pd modified TiO2 nanofiber catalyst for carbon-carbon coupling Heck reaction. J. Nanomater., 2017,. Article ID 8290892.
[http://dx.doi.org/10.1155/2017/8290892]
[44]
Cookson, J. The preparation of palladium nanoparticles. Platin. Met. Rev., 2012, 56(2), 83-98.
[http://dx.doi.org/10.1595/147106712X632415]
[45]
Balanta, A.; Godard, C.; Claver, C. Pd nanoparticles for C-C coupling reactions. Chem. Soc. Rev., 2011, 40(10), 4973-4985.
[http://dx.doi.org/10.1039/c1cs15195a] [PMID: 21879073]
[46]
Du, Q.; Li, Y. Air-stable, recyclable, and time-efficient diphenylphosphinite cellulose-supported palladium nanoparticles as a catalyst for Suzuki-Miyaura reactions. Beilstein J. Org. Chem., 2011, 7, 378-385.
[http://dx.doi.org/10.3762/bjoc.7.48] [PMID: 21512591]
[47]
Erami, R.S.; Garcia, D.D.; Prashar, S.; Dieguez, A.R.; Fajardo, M.; Amirnasr, M.; Ruiz, S.G. Suzuki-Miyaura C-C coupling reactions catalyzed by supported pd nanoparticles for the preparation of fluorinated biphenyl derivatives. Catalysts, 2017, 7(3), 76.
[http://dx.doi.org/10.3390/catal7030076]
[48]
Li, Y.; Xu, L.; Xu, B.; Mao, Z.; Xu, H.; Zhong, Y.; Zhang, L.; Wang, B.; Sui, X. Cellulose sponge supported palladium nanoparticles as recyclable cross-coupling catalysts. ACS Appl. Mater. Interfaces, 2017, 9(20), 17155-17162.
[http://dx.doi.org/10.1021/acsami.7b03600] [PMID: 28471160]
[49]
Budroni, G.; Corma, A.; Garcia, H.; Primo, A. Pd nanoparticles embedded in sponge-like porous silica as a Suzuki-Miyaura catalyst: Similarities and differences with homogeneous catalysts. J. Catal., 2007, 251(2), 345-353.
[http://dx.doi.org/10.1016/j.jcat.2007.07.027]
[50]
Xia, Y.; Mokaya, R. Generalized and facile synthesis approach to n-doped highly graphitic mesoporous carbon materials. Chem. Mater., 2005, 17(6), 1553-1560.
[http://dx.doi.org/10.1021/cm048057y]
[51]
Yoon, H.; Ko, S.; Jang, J. Nitrogen-doped magnetic carbon nanoparticles as catalyst supports for efficient recovery and recycling. Chem. Commun. (Camb.), 2007, 14(14), 1468-1470.
[http://dx.doi.org/10.1039/b616660a] [PMID: 17389995]
[52]
Sharma, V.; Kumar, S.; Bahuguna, A.; Gambhir, D.; Sagara, P.S.; Krishnan, V. Plant leaves as natural green scaffolds for palladium catalyzed Suzuki-Miyaura coupling reactions. Bioinspir. Biomim., 2017, 12.
[PMID: 28000624]
[53]
Zharmagambetovaa, A.K.; Seitkalievaa, K.S.; Talgatova, E.T.; Auezkhanovaa, A.S.; Dzhardimalievab, G.I.; Pomogailob, A.D. Polymer modified supported palladium catalysts for the hydrogenation of acetylene compounds. Kinet. Catal., 2016, 57(3), 360-367.
[http://dx.doi.org/10.1134/S0023158416030174]
[54]
Mansour, A.; Kehat, T.; Portnoy, M. Dendritic effects in catalysis by Pd complexes of bidentate phosphines on a dendronized support: Heck vs. carbonylation reactions. Org. Biomol. Chem., 2008, 6(18), 3382-3387.
[http://dx.doi.org/10.1039/b809715a] [PMID: 18802646]
[55]
Karami, K.; Moghadam, Z.K.; Kharat, M.H. Polyethylene glycol supported recyclable nc palladacycle catalyst for Heck cross coupling reactions. Catal. Commun., 2014, 43, 25-28.
[http://dx.doi.org/10.1016/j.catcom.2013.08.027]
[56]
Tamami, B.; Allahyari, H.; Ghasemi, S.; Farjadian, F. Palladium nanoparticles supported on poly (n-vinylpyrrolidone)-grafted silica as new recyclable catalyst for heck cross-coupling reactions. J. Organomet. Chem., 2011, 696, 594-599.
[http://dx.doi.org/10.1016/j.jorganchem.2010.09.028]
[57]
Tamami, B.; Farjadian, F.; Ghasemi, S.; Allahyari, H.; Mirzadeh, M. Palladium nanoparticles supported on poly(n-vinylpyrrolidone)-grafted silica as an efficient catalyst for copper-free Sonogashira and Suzuki cross-coupling reactions. J. Brazil. Chem. Soc., 2015, 26(8), 1591-1598.
[http://dx.doi.org/10.5935/0103-5053.20150129]
[58]
Hariprasad, E.; Radhakrishnan, T.P. Palladium nanoparticle-embedded polymer thin film “dip catalyst” for Suzuki-Miyaura reaction. ACS Catal., 2012, 2, 1179-1186.
[http://dx.doi.org/10.1021/cs300158g]
[59]
Qi, S.U.N.; Feng, Z.H.U.L.; Hua, S.U.N.Z.; Xiang, M.E.N.G.; Shou, X.I.A.O.F. Porous polymer supported palladium catalyst for cross coupling reactions with high activity and recyclability. Sci. China Chem., 2012, 55(10), 2095-2103.
[http://dx.doi.org/10.1007/s11426-011-4491-8]
[60]
Colombel, V.; Presset, M.; Oehlrich, D.; Rombouts, F.; Molander, G.A. Synthesis and reactivity of solid-supported organotrifluoroborates in Suzuki cross-coupling. Org. Lett., 2012, 14(7), 1680-1683.
[http://dx.doi.org/10.1021/ol300215p] [PMID: 22404451]
[61]
Yang, P.; Ma, R.; Bian, F. Palladium supported on metformin functionalized magnetic polymer nanocomposites: A highly efficient and reusable catalyst for the suzuki-miyaura coupling reaction. ChemCatChem, 2016, 8, 3746-3754.
[http://dx.doi.org/10.1002/cctc.201600994]
[62]
Ma, R.; Yang, P.; Bian, F. Magnetic dendritic polymer nanocomposites as supports for palladium: A highly efficient and reusable catalyst for Mizoroki-Heck and Suzuki-Miyaura coupling reactions. ChemCatChem, 2013, 8(24), 1-3.
[63]
Aghaei, E.; Alorro, R.D.; Encila, A.N.; Yoo, K. Magnetic adsorbents for the recovery of precious metals from leach solutions and waste water. Metals (Basel), 2017, 7(12), 529.
[64]
Giakisikli, G.; Anthemidis, A.N. Magnetic materials as sorbents for metal/metalloid preconcentration and/or separation. A review. Anal. Chim. Acta, 2013, 789, 1-16.
[http://dx.doi.org/10.1016/j.aca.2013.04.021] [PMID: 23856225]
[65]
Sydnes, M.O. The use of palladium on magnetic support as catalyst for suzuki-miyaura cross-coupling reactions. Catalysts, 2017, 7(1), 35.
[http://dx.doi.org/10.3390/catal7010035]
[66]
Lopes, J.L.; Marques, K.L.; Girão, A.V.; Pereira, E.; Trindade, T. Functionalized magnetite particles for adsorption of colloidal noble metal nanoparticles. J. Colloid Interface Sci., 2016, 475, 96-103.
[http://dx.doi.org/10.1016/j.jcis.2016.04.046] [PMID: 27156089]
[67]
Anbia, M.; Mehrizi, R. Separation and recovery of platinum by magnetic core-shell nanostructures modified with n-(2-aminoethyl)-3-aminopropyltrimethoxysilane. J. Appl. Chem. Res., 2016, 10, 39-49.
[68]
Kraus, A.; Jainae, K.; Unob, F.; Sukpirom, N. Synthesis of MPTS modified cobalt ferrite nanoparticles and their adsorption properties in relation to Au(III). J. Colloid Interface Sci., 2009, 338(2), 359-365.
[http://dx.doi.org/10.1016/j.jcis.2009.06.045] [PMID: 19647836]
[69]
Wang, P.; Cai, P.; Chen, J.; Ji, M. Agarose-alumina composite supported palladium catalyst for Suzuki coupling reactions. J. Braz. Chem. Soc., 2015, 26(4), 748-754.
[http://dx.doi.org/10.5935/0103-5053.20150036]
[70]
Basu, B.; Paul, S. Solid-phase organic synthesis and catalysis: some recent strategies using alumina, silica, and polyionic resins. J. Catal., 2013, 2013, Article ID 614829.
[http://dx.doi.org/10.1155/2013/614829]
[71]
Rifai, N.A.; Miedziak, P.J.; Morad, M.; Sankar, M.; Waldron, C.; Cattaneo, S.; Cao, E.; Pattisson, S.; Morgan, D.; Bethell, D.; Hutchings, G.J.; Gavriilidis, A. Deactivation behavior of supported gold palladium nanoalloy catalysts during the selective oxidation of benzyl alcohol in a micro-packed bed reactor. Ind. Eng. Chem. Res., 2017, 56, 12984-12993.
[http://dx.doi.org/10.1021/acs.iecr.7b01159]
[72]
Djakovitch, L.; Rollet, P. Sonogashira cross-coupling reactions catalysed by heterogeneous copper-free pd-zeolites. Tetrahedron Lett., 2004, 1367-1370
[http://dx.doi.org/10.1016/j.tetlet.2003.12.077]
[73]
Opanasenko, M.; Stepnicka, P.; Cejka, J. Heterogeneous Pd catalysts supported on silica matrices. RSC Advances, 2014, 4, 65137-65162.
[http://dx.doi.org/10.1039/C4RA11963K]
[74]
Ghasemi, S.; Karim, S. Mizoroki-Heck cross-coupling reaction of haloarenes mediated by a well-controlled modified polyacrylamide brush grafted silica/pd nanoparticle system. Bull. Chem. Soc. Jpn., 2017, 90, 485-490.
[http://dx.doi.org/10.1246/bcsj.20160374]
[75]
Jalilian, N.; Ebrahimzadeh, H.; Asgharinezhad, A.A.; Molaei, K. Extraction and determination of trace amounts of gold(III), palladium(II), platinum(II) and silver(I) with the aid of a magnetic nanosorbent made from Fe3O4-decorated and silica-coated graphene oxide modified with a polypyrrole polythiophene copolymer. Mikrochim. Acta, 2017, 184, 2191-2200.
[http://dx.doi.org/10.1007/s00604-017-2170-y]
[76]
Scheuermann, G.M.; Rumi, L.; Steurer, P.; Bannwarth, W.; Mülhaupt, R. Palladium nanoparticles on graphite oxide and its functionalized graphene derivatives as highly active catalysts for the Suzuki-Miyaura coupling reaction. J. Am. Chem. Soc., 2009, 131(23), 8262-8270.
[http://dx.doi.org/10.1021/ja901105a] [PMID: 19469566]
[77]
Fairlamb, I.J.S. Transition metals in organic synthesis: Cross-coupling, C-H activation processes and cyclisation strategies. Annu. Rep. Prog. Chem. Sect (B), 2007, 103, 68-89.
[http://dx.doi.org/10.1039/b614710k]
[78]
Miyaura, N.; Suzuki, A. Palladium-Catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev., 1995, 95, 2457-2483.
[http://dx.doi.org/10.1021/cr00039a007]
[79]
Dai, W.; Xiao, J.; Jin, G.; Wu, J.; Cao, S. Palladium- and nickel-catalyzed Kumada cross-coupling reactions of gem-difluoroalkenes and monofluoroalkenes with Grignard reagents. J. Org. Chem., 2014, 79(21), 10537-10546.
[http://dx.doi.org/10.1021/jo5022234] [PMID: 25327183]
[80]
Phapale, V.B.; Cárdenas, D.J. Nickel-catalysed Negishi cross-coupling reactions: Scope and mechanisms. Chem. Soc. Rev., 2009, 38(6), 1598-1607.
[http://dx.doi.org/10.1039/b805648j] [PMID: 19587955]
[81]
Li, H.; Seechurn, J.C.C.C.; Colacot, T.J. Development of preformed Pd Catalysts for cross-coupling reactions, beyond the 2010 Nobel prize. ACS Catal., 2012, 2, 1147-1164.
[http://dx.doi.org/10.1021/cs300082f]
[82]
Beletskaya, I.P.; Cheprakov, A.V. The heck reaction as a sharpening stone of palladium catalysis. Chem. Rev., 2000, 100(8), 3009-3066.
[http://dx.doi.org/10.1021/cr9903048] [PMID: 11749313]
[83]
Dobrounig, P.; Trobe, M.; Breinbauer, R. Sequential and iterative Pd-catalyzed cross-coupling reactions in organic synthesis. Monatsh. Chem., 2017, 148(1), 3-35.
[http://dx.doi.org/10.1007/s00706-016-1883-7] [PMID: 28127089]
[84]
Wang, G.Z.; Shang, R.; Cheng, W.M.; Fu, Y. Irradiation-induced Heck reaction of inactivated alkyl halides at room temperature. J. Am. Chem. Soc., 2017, 139(50), 18307-18312.
[http://dx.doi.org/10.1021/jacs.7b10009] [PMID: 29116777]
[85]
Jagtap, S. Heck reaction-state of the art. Catal., 2017, 7(9), 267.
[http://dx.doi.org/10.3390/catal7090267]
[86]
Singh, S.; Bruffaerts, J.; Vasseur, A.; Marek, I. A unique Pd-catalysed Heck arylation as a remote trigger for cyclopropane selective ring-opening. Nat. Commun., 2017, 8, 14200.
[http://dx.doi.org/10.1038/ncomms14200] [PMID: 28169276]
[87]
Carson, F.; Pascanu, V.; Bermejo Gómez, A.; Zhang, Y.; Platero-Prats, A.E.; Zou, X.; Martín-Matute, B. Influence of the base on Pd@MIL-101-NH2(Cr) as a catalyst for the Suzuki-Miyaura cross-coupling reaction. Chemistry, 2015, 21(30), 10896-10902.
[http://dx.doi.org/10.1002/chem.201500843] [PMID: 26100552]
[88]
Fernández, F.; Cordero, B.; Durand, J.; Muller, G.; Malbosc, F.; Kihn, Y.; Teuma, E.; Gómez, M. Palladium catalyzed Suzuki C-C couplings in an ionic liquid: Nanoparticles responsible for the catalytic activity. Dalton Trans., 2007, (47), 5572-5581.
[http://dx.doi.org/10.1039/b713449e] [PMID: 18043820]
[89]
Sharma, P.; Rohilla, S.; Jain, N. Palladium catalyzed carbonylative coupling synthesis of arylketones and arylesters using chloroform as the carbon monoxide source. J. Org. Chem., 2017, 82(2), 1105-1113.
[http://dx.doi.org/10.1021/acs.joc.6b02711] [PMID: 28001401]
[90]
Netherton, M.R.; Fu, G.C. Nickel-catalyzed cross-couplings of unactivated alkyl halides and pseudohalides with organometallic compounds. Adv. Synth. Catal., 2004, 346, 1525-1532.
[http://dx.doi.org/10.1002/adsc.200404223]
[91]
Payard, P.A.; Perego, L.A.; Ciofini, I.; Grimaud, L. Taming nickel catalyzed Suzuki-Miyaura coupling: A mechanistic focus on boron to- nickel transmetalation. Catal., 2018, 8, 4812-4823.
[http://dx.doi.org/10.1021/acscatal.8b00933]
[92]
Budnikova, Y.H.; Vicic, D.A.; Klein, A. Exploring mechanisms in Ni terpyridine catalyzed C-C cross-coupling reactions-A review. Inorg., 2018, 6(1), 1-18s.
[http://dx.doi.org/10.3390/inorganics6010018]
[93]
Dai, W.M.; Zhang, Y. Homogeneous catalysis for unreactive bond activation. Tetrahedron Lett., 2005, 46, 1377-1381.
[http://dx.doi.org/10.1016/j.tetlet.2004.12.133]
[94]
Walker, S.D.; Barder, T.E.; Martinelli, J.R.; Buchwald, S.L. A rationally designed universal catalyst for Suzuki-Miyaura coupling processes. Angew. Chem. Int. Ed. Engl., 2004, 43(14), 1871-1876.
[http://dx.doi.org/10.1002/anie.200353615] [PMID: 15054800]
[95]
Wolf, C.; Kovi, K.E. Palladium-catalyzed Suzuki-Miyaura cross coupling using phosphinous acids and Dialkyl(Chloro)phosphane ligands. Eur. J. Org. Chem., 2006, 1917-1925.
[http://dx.doi.org/10.1002/ejoc.200500843]
[96]
Ozdemir, I.; Yaşar, S.; Demir, S.; Çetinkaya, B. Suzuki reaction of aryl chlorides using saturated N‐heterocarbene ligands. Heteroatom Chem., 2005, 16, 557-561.
[http://dx.doi.org/10.1002/hc.20140]
[97]
O’Brien, C.J.; Kantchev, E.A.B.; Valente, C.; Hadei, N.; Chass, G.A.; Lough, A.; Hopkinson, A.C.; Organ, M.G. Easily prepared air- and moisture-stable Pd-NHC (NHC=N-heterocyclic carbene) complexes: A reliable, user-friendly, highly active palladium precatalyst for the Suzuki-Miyaura reaction. Chemistry, 2006, 12(18), 4743-4748.
[http://dx.doi.org/10.1002/chem.200600251] [PMID: 16568494]
[98]
Uozumi, Y. Recent progress in polymeric palladium catalysts for organic synthesis. Top. Curr. Chem., 2004, 242, 77-112.
[http://dx.doi.org/10.1007/b96874] [PMID: 23900911]
[99]
Lamblin, M.; Hardy-Nassar, L.; Hierso, J.C.; Fouquet, E.; Felpin, F.X. Recyclable heterogeneous palladium catalysts in pure water: Sustainable developments in Suzuki, Heck, Sonogashira and Tsuji-Trost reactions. Adv. Synth. Catal., 2010, 352, 33-79s.
[http://dx.doi.org/10.1002/adsc.200900765]
[100]
Nan, G.; Ren, F.; Luo, M. Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst. Beilstein J. Org. Chem., 2010, 6(70), 70.
[http://dx.doi.org/10.3762/bjoc.6.70] [PMID: 20703375]
[101]
Barbeiro, C.S.; Vasconcelos, S.N.S.; Oliveira, I.M.D.; Schpector, J.Z.; Caracelli, D.; Maganhi, S.H.; Stefani, H.L.A. Suzuki-Miyaura cross-coupling reaction catalyzed by palladium complexes of hydroxynaphthalene-2-oxazolines. Chem. Select., 2017, 2, 8173-8177.
[http://dx.doi.org/10.1002/slct.201701197]
[102]
Alonso, D.A.; Baeza, A.; Chinchilla, R.; Gomez, C.; Guillena, G.; Pastor, I.M.; Ramon, D.J. Solid-Supported palladium catalysts in sonogashira reactions: Recent developments. Catal., 2018, 8, 202.
[http://dx.doi.org/10.3390/catal8050202]
[103]
Monguchi, Y.; Wakayama, F.; Ueda, S.; Ito, R.; Takada, H.; Inoue, H.; Nakamura, A.; Sawama, Y.; Sajiki, H. Amphipathic monolith supported palladium catalysts for chemoselective hydrogenation and cross-coupling reactions. RSC Advances, 2017, 7, 1833-1840.
[http://dx.doi.org/10.1039/C6RA24769E]
[104]
Blangetti, M.; Rosso, H.; Prandi, C.; Deagostino, A.; Venturello, P. Suzuki-miyaura cross-coupling in acylation reactions, scope and recent developments. Molecules, 2013, 18(1), 1188-1213.
[http://dx.doi.org/10.3390/molecules18011188] [PMID: 23344208]
[105]
Roy, D.; Uozumi, Y. recent advances in palladium-catalyzed cross coupling reactions at ppm to ppb molar catalyst loadings. Adv. Synth. Catal., 2017, 360(4)
[http://dx.doi.org/10.1002/adsc.201700810]
[106]
Hussain, I.; Capricho, J.; Yawer, M.A. Synthesis of biaryls via ligand-free Suzuki-Miyaura cross-coupling reactions: A review of homogeneous and heterogeneous catalytic developments. Adv. Synth. Catal., 2016, 358(21), 3320-3349.
[http://dx.doi.org/10.1002/adsc.201600354]
[107]
Mamane, V. metal-catalyzed cross-coupling reactions for ferrocene functionalization: Recent applications in synthesis, material science and asymmetric catalysis. Org. Chem., 2008, 5, 303-312.
[http://dx.doi.org/10.2174/157019308786242160]
[108]
Hajipour, A.R.; Rezaeia, F.; Khorsandia, Z. Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst. Green Chem., 2017, 19, 1353-1361.
[http://dx.doi.org/10.1039/C6GC03377F]
[109]
Yong, L.; Yao, M.L.; Blevins, D.W.; Kabalka, G.W. Synthesis of PEG-supported organotrifluoroborates and their applications in palladium-catalyzed homo-coupling reactions. Dalton Trans., 2015, 44(10), 4759-4764.
[http://dx.doi.org/10.1039/C4DT03492A] [PMID: 25665712]
[110]
Jeffery, T. Palladium-catalysed vinylation of organic halides under solid-liquid phase transfer conditions. J. Chem. Soc. Chem. Commun., 1984, 1287-1289
[http://dx.doi.org/10.1039/C39840001287]
[111]
Shaikh, T.M.; Hong, F.E. Palladium(II)-catalyzed Heck reaction of aryl halides and arylboronic acids with olefins under mild conditions. Beilstein J. Org. Chem., 2013, 9, 1578-1588.
[http://dx.doi.org/10.3762/bjoc.9.180] [PMID: 23946858]
[112]
Yao, Q.; Kinney, E.P.; Yang, Z. Ligand-free Heck reaction: Pd(OAc)2 as an active catalyst revisited. J. Org. Chem., 2003, 68(19), 7528-7531.
[http://dx.doi.org/10.1021/jo034646w] [PMID: 12968913]
[113]
Leyva-Pérez, A.; Oliver-Meseguer, J.; Rubio-Marqués, P.; Corma, A. Water-stabilized three- and four-atom palladium clusters as highly active catalytic species in ligand-free C-C cross-coupling reactions. Angew. Chem. Int. Ed. Engl., 2013, 52(44), 11554-11559.
[http://dx.doi.org/10.1002/anie.201303188] [PMID: 24038914]
[114]
Shi, W.; Yu, J.; Jiang, Z.; Shao, Q.; Su, W. Encaging palladium(0) in layered double hydroxide: A sustainable catalyst for solvent-free and ligand-free Heck reaction in a ball mill. Beilstein J. Org. Chem., 2017, 13, 1661-1668.
[http://dx.doi.org/10.3762/bjoc.13.160] [PMID: 28904609]
[115]
Sołoducho, J.; Olech, K.; Swist, A.; Zając, D.; Cabaj, J. Recent advances of modern protocol for C-C bonds-The Suzuki cross coupling. Adv. Chem. Eng. Sci., 2013, 3, 19-32.
[http://dx.doi.org/10.4236/aces.2013.33A1003]
[116]
Maluenda, I.; Navarro, O. Recent developments in the Suzuki-Miyaura reaction: 2010-2014. Molecules, 2015, 20(5), 7528-7557.
[http://dx.doi.org/10.3390/molecules20057528] [PMID: 25919276]
[117]
Cabri, W.; Candiani, I. Recent developments and new perspectives in the Heck reaction. Acc. Chem. Res., 1995, 28, 2-7.
[http://dx.doi.org/10.1021/ar00049a001]
[118]
Lee, H.S.; Pai, S.H.; Liao, W.T.; Yang, X.J.; Tsai, F.Y. Mono and double Mizoroki-Heck reaction of aryl halides with dialkyl vinylphosphonates using a reusable palladium catalyst under aqueous medium. RSC Advances, 2017, 7, 34293-34299.
[http://dx.doi.org/10.1039/C7RA06464K]
[119]
Asachenko, A.F.; Sorochkina, K.R.; Dzhevakov, P.B.; Topchiy, M.A.; Nechaev, M.S. Suzuki-Miyaura cross-coupling under solvent-free conditions. Adv. Synth. Catal., 2013, 355, 3553-3557.
[http://dx.doi.org/10.1002/adsc.201300741]
[120]
Liang, Q.; Xing, P.; Huang, Z.; Dong, J.; Sharpless, K.B.; Li, X.; Jiang, B. Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates. Org. Lett., 2015, 17(8), 1942-1945.
[http://dx.doi.org/10.1021/acs.orglett.5b00654] [PMID: 25856416]
[121]
Paul, S.; Islam, M.M.; Islam, S.M. Suzuki-Miyaura reaction by heterogeneously supported Pd in water: recent studies. RSC Advances, 2015, 5, 42193-42221.
[http://dx.doi.org/10.1039/C4RA17308B]
[122]
Dewan, A. A highly efficient and inexpensive palladium-salen complex for room temperature Suzuki-Miyaura reaction. Bull. Korean Chem. Soc., 2014, 35(6), 1855-1858.
[http://dx.doi.org/10.5012/bkcs.2014.35.6.1855]
[123]
Jadhav, S.N.; Kumbhar, A.S.; Rode, C.V.; Salunkhe, R.S. Ligand free Pd catalyzed cross-coupling reactions in an aqueous hydrotropic medium. Green Chem., 2016, 18, 1898-1911.
[http://dx.doi.org/10.1039/C5GC02314A]
[124]
Chatterjee, A.; Ward, T.R. Recent advances in the palladium catalyzed Suzuki-Miyaura cross-coupling reaction in water. Catal. Lett., 2016, 146, 820-840.
[http://dx.doi.org/10.1007/s10562-016-1707-8]
[125]
Jadhav, S.N.; Rode, C.V. An efficient palladium catalyzed Mizoroki-Heck cross-coupling in water. Green Chem., 2017, 19, 5958-5970.
[http://dx.doi.org/10.1039/C7GC02869E]
[126]
Masllorens, J.; Gonzalez, I.; Roglans, A. Recoverable homogeneous palladium(0) catalyst for cross-coupling reactions of arenediazonium salts with potassium organotrifluoroborates: Detection of catalytic intermediates by electrospray ionization mass spectrometry. Eur. J. Org. Chem., 2007, 158-166.
[http://dx.doi.org/10.1002/ejoc.200600600]
[127]
Suzuka, T.; Kimura, K.; Nagamine, T. Reusable polymer-supported terpyridine palladium complex for Suzuki-Miyaura, Mizoroki-Heck, Sonogashira, and Tsuji-Trost reaction in water. Polymers (Basel), 2011, 3, 621-639.
[http://dx.doi.org/10.3390/polym3010621]
[128]
Tamang, S.R.; Hoefelmeyer, J.D. Chloro(2-[mesityl(quinolin-8-yl-κN)boryl]-3,5-dimethyl-phenylmethyl-κC)palladium(II) as a catalyst for Heck reactions. Molecules, 2015, 20(7), 12979-12991.
[http://dx.doi.org/10.3390/molecules200712979] [PMID: 26193250]
[129]
Bernhardt, F.; Trotzki, R.; Szuppa, T.; Stolle, A.; Ondruschka, B. Solvent-free and time-efficient Suzuki-Miyaura reaction in a ball mill: The solid reagent system KF-Al2O3 under inspection. Beilstein J. Org. Chem., 2010, 6(7), 7.
[http://dx.doi.org/10.3762/bjoc.6.7] [PMID: 20485589]
[130]
Mondal, M.; Bora, U. An efficient protocol for palladium-catalyzed ligand-free Suzuki-Miyaura coupling in water. Green Chem., 2011, 14, 1873-1876.
[http://dx.doi.org/10.1039/c2gc35401b]
[131]
Holmes, A.B.; Early, T.R.; Gordon, R.S.; Stamp, L.M. Carbon dioxide as a solvent for polymerization and cross coupling reactions. Fuel Chem. Div. Preprints, 2002, 47(1), 282-283.
[132]
Toche, R.; Janrao, R. An efficient microwave-assisted Suzuki cross-coupling reactions on quinoline derivatives in water and study the electronic effects thereof Inter. J. Sci. Res. Pub, 2013, 3(8)
[133]
Xia, M.; Wang, Y.G. A novel microwave-activated Sonogashira coupling reaction and cleavage using polyethylene glycol as phase transfer catalyst and polymer support. J. Chem. Res., 2002, 173-175
[http://dx.doi.org/10.3184/030823402103171564]
[134]
Martinez, A.V.; Invernizzi, F.; Leal, A.; Mayoral, J.A.; Garcia, J.I. Microwaves-promoted solventless Mizoroki-Heck reactions catalysed by Pd nanoparticles supported on laponite clay. RSC Advances, 2015, 5, 10102-10109.
[http://dx.doi.org/10.1039/C4RA15418E]
[135]
Hua, K.E.H.; Feng, C.X.; Yuan, F.Y.; Gang, Z.O.U. Highly efficient nickel/phosphine catalyzed cross-couplings of diarylborinic acids with aryl tosylates and sulfamates. Sci. China Chem., 2014, 57(8)
[136]
Desrosiers, J.N.; Wen, J.; Tcyrulnikov, S.; Biswas, S.; Qu, B.; Hie, L.; Kurouski, D.; Wu, L.; Grinberg, N.; Haddad, N.; Busacca, C.A.; Yee, N.K.; Song, J.J.; Garg, N.K.; Zhang, X.; Kozlowski, M.C.; Senanayake, C.H. Enantioselective nickel-catalyzed Mizoroki-Heck cyclizations to generate quaternary stereocentre. Org. Lett., 2017, 19(13), 3338-3341.
[http://dx.doi.org/10.1021/acs.orglett.7b01054] [PMID: 28604006]
[137]
Ge, S.; Hartwig, J.F. Highly reactive, single-component nickel catalyst precursor for Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides. Angew. Chem. Int. Ed. Engl., 2012, 51(51), 12837-12841.
[http://dx.doi.org/10.1002/anie.201207428] [PMID: 23136047]
[138]
Jezorek, R.L.; Zhang, N.; Leowanawat, P.; Bunner, M.H.; Gutsche, N.; Pesti, A.K.R.; Olsen, J.T.; Percec, V. Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature. Org. Lett., 2014, 16(24), 6326-6329.
[http://dx.doi.org/10.1021/ol503061c] [PMID: 25467653]
[139]
Goudarzian, N.; Gholinejad, M.; Ghahramani, P. Recyclable nickel catalysed Suzuki-Miyaura reaction in the presence of polyethyleneimine under phosphine-free conditions in ethylene glycol. J. Chem. Sci., 2011, 123(4), 485-489.
[http://dx.doi.org/10.1007/s12039-011-0092-5]
[140]
Muto, K.; Yamaguchi, J.; Musaev, D.G.; Itami, K. Decarbonylative organoboron cross-coupling of esters by nickel catalysis. Nat. Commun., 2015, 6, 7508.
[141]
Tobisu, M.; Xu, T.; Shimasaki, T.; Chatani, N. Nickel-catalyzed Suzuki-Miyaura reaction of aryl fluorides. J. Am. Chem. Soc., 2011, 133(48), 19505-19511.
[http://dx.doi.org/10.1021/ja207759e] [PMID: 22023167]
[142]
Zhou, J.; Berthel, J.H.J.; Kuntze-Fechner, M.W.; Friedrich, A.; Marder, T.B.; Radius, U. NHC-nickel-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl boronate esters with perfluorobenzenes. J. Org. Chem., 2016, 81(13), 5789-5794.
[http://dx.doi.org/10.1021/acs.joc.6b01041] [PMID: 27254478]
[143]
Cherney, A.H.; Reisman, S.E. Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles. J. Am. Chem. Soc., 2014, 136(41), 14365-14368.
[http://dx.doi.org/10.1021/ja508067c] [PMID: 25245492]
[144]
Kalbasi, R.J.; Mosaddegh, N. Suzuki-Miyaura cross-coupling reaction catalyzed by nickel nanoparticles supported on Poly(N-Vinyl-2-Pyrrolidone)/TiO2-ZrO2 Composite. Bull. Korean Chem. Soc., 2011, 32(8)
[http://dx.doi.org/10.5012/bkcs.2011.32.8.2584]
[145]
Lhermet, R.; Durandetti, M.; Maddaluno, J. Intramolecular carbonickelation of alkenes. Beilstein J. Org. Chem., 2013, 9, 710-716.
[http://dx.doi.org/10.3762/bjoc.9.81] [PMID: 23766783]
[146]
Lin, B.L.; Liu, L.; Fu, Y.; Luo, S.W.; Chen, Q.; Xiang, Q. Comparing nickel and palladium-catalyzed Heck reactions. Organometallics, 2004, 23, 2114-2123.
[http://dx.doi.org/10.1021/om034067h]
[147]
Tasker, S.Z.; Standley, E.A.; Jamison, T.F. Recent advances in homogeneous nickel catalysis. Nature, 2014, 509(7500), 299-309.
[http://dx.doi.org/10.1038/nature13274] [PMID: 24828188]
[148]
Lu, D.D.; He, X.X.; Liu, F.S. Bulky yet flexible Pd-Peppsi-Ipentan for the synthesis of sterically hindered biaryls in air. J. Org. Chem., 2017, 82(20), 10898-10911.
[http://dx.doi.org/10.1021/acs.joc.7b01711] [PMID: 28925697]
[149]
Yamaguchi, J.; Muto, K.; Itami, K. Recent progress in nickel catalyzed biaryl coupling. Eur. J. Org. Chem., 2012.
[150]
Negishi, E. Palladium or nickel-catalyzed cross coupling - A new selective method for carbon-carbon bond formation. Acc. Chem. Res., 1982, 15, 340-348.
[http://dx.doi.org/10.1021/ar00083a001]
[151]
Suzuki, A.; Yamamoto, Y. Cross-coupling reactions of organoboranes: An easy method for C-C bonding. Chem. Lett., 2011, 40, 894-90.
[http://dx.doi.org/10.1246/cl.2011.894]
[152]
Chinchilla, R.; Nájera, C. Recent advances in Sonogashira reactions. Chem. Soc. Rev., 2011, 40(10), 5084-5121.
[http://dx.doi.org/10.1039/c1cs15071e] [PMID: 21655588]
[153]
Gujral, S.S.; Khatri, S.; Riyal, P. Suzuki cross coupling reaction- A review. Indo. Glo. J. Pharm. Sci., 2012, 2(4), 351-367.
[154]
Suzuki, A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles. J. Organomet. Chem., 1999, 576, 147-168.
[http://dx.doi.org/10.1016/S0022-328X(98)01055-9]


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 17
ISSUE: 5
Year: 2020
Published on: 11 August, 2020
Page: [589 - 604]
Pages: 16
DOI: 10.2174/1570193X16666190617160339
Price: $65

Article Metrics

PDF: 24
HTML: 2
PRC: 1



Most Downloaded Article(s)